The instant invention provides substituted methyl isopropyl oxocyclohexane derivatives which are novel, defined according to the structure: ##STR17## wherein the moiety represents one of the structures: ##STR18## wherein when the moiety X has the structure: ##STR19## then one of the lines: EQU [++++]
is a carbon-carbon double bond and the other of the lines: EQU [++++]
is a carbon-carbon single bond and when the moiety X has the structure: ##STR20## then both of the lines: EQU [++++]
represent carbon-carbon single bonds;
wherein, one of R.sub.1, R.sub.2 and R.sub.3 represent 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:
and uses of said substituted methyl isopropyl oxocyclohexane derivatives for their organoleptic properties in augmenting or enhancing the aroma of perfume compositions, perfumed articles or colognes.
Chemical compounds which can provide herbaceous, woody, earthy, camphoraceous, tabac-resin-like, guiacwood-like, cardamom, jute-like, spicy, honey, sweaty, ionone-like, smokey, rosey, vetiver-like, fruity and musky aroma nuances are highly desirable in the art of perfumery. Many of the natural materials which provides such fragrances and contribute such desired nuances to perfumery compositions are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance, or augment the essential fragrance notes provided by natural essential oils or compositions thereof.
The fundamental problem in creating artificial fragrance agents is that the artificial fragrance to be achieved to be as natural as possible. This generally proves to be a difficult task since the mechanism for a fragrance development in many fragrance materials is not completely known. This is noticeable in products in the fragrance area having herbaceous, woody, earthy, camphoraceous, tobacco resin-like, guiacwood-like, cardamom, jute-like, spicy, honey, sweaty, ionone-like, smokey, rosey, vetiver-like, fruity and musky aroma nuances.
The substituted methyl isopropyl oxocyclohexane derivatives of my invention are not known in the prior art. Although substituted alkyl isopropyl cyclohexanones are known in the prior art, the disclosure of such compounds does not include the utilization thereof in perfumery and, furthermore, does not include processes for producing the substituted alkyl isopropyl cyclohexanones of my invention. Wiemann, et al and Riand and Brun in the references:
(i) Wiemann, et al, Ann. Chim., 1972, Volume 7, pages 399-499, title: "Contributions a L'Etrude des Mechanismes de Condensations Catalytiques de Cetones .beta.-Alkyl .alpha.-Ethyleniques en Milieu Heterogene et en Phase Vapeur. Etudes Spectrographiques IR, UV, RMN". PA0 (ii) Riand and Brun, Bulletin de la Societe Chimique de France, 1976, Nos. 3-4 (combined) pages 557-562 inclusive, title: "No. 105--Spectrometrie de Masse. II--Fragmentations Induites par Impact Electronique de Cyclohexenones".
disclose the compounds having the structures: ##STR21## produced by dimerization of the compound having the structure: ##STR22## over magnesium oxide dimerization catalyst in the gas phase according to the reaction: ##STR23##
The prior art process of Riand and Brun or Wiemann, et al does not utilize a liquid phase dimerization and does not utilize the catalyst systems of my invention nor does it carry out a reduction of the resultant cyclohexanone. Furthermore, the reaction mixture produced by Riand and Brun or Wiemann does not give rise to the same mixture of compounds which is the starting material for my invention.
Unsaturated cyclic ketones with unsaturated alkylene and alkylidene side chains are known in the field of perfumery; and unsaturated cyclic alkanols and alkanol acetates with unsaturated alkylene and alkylidene side chains are also known in the art of perfumery but these compounds are different in kind in structure from the structures of the compounds of the present invention.
Thus, laevo-carvyl acetate having the structure: ##STR24## is disclosed by Arctander, "Perfume and Flavor Chemicals (Aroma Chemicals)" at Monograph No. 582 to have a refreshing, green-minty, spearmint-like odor, more "cool" than carvone, not as penetrating but with a peculiar "metallic" undertone . . . sweet, spicy-minty, green and refreshing taste not as powerful as carvone but overall more pleasant, versatile in character". Arctander further states at Monograph No. 578 that laevo-carveol having the structure: ##STR25## has an odor which is "more caraway-like than spearmint-like (according to the majority of opinions)". Arctander further states that Monograph No. 2770 that iso-pulegone having the structure: ##STR26## has a "powerful minty, woody, mildly green odor . . . very diffusive and penetrating, not as sweet as pulegone, not as tenacious".
Nothing in the prior art discloses the novel and useful and unexpectedly advantageous organoleptic utilities of the compounds of my invention and nothing in the prior art discloses or renders obvious the novel compounds of my invention or the novel products-by-process of my invention.